Kent Island

Kent Island has a rich history dating back to 1631, when William Claiborne of Jamestown first set up a trading post on the island. It is said that Claiborne liked being on Kent Island so much that he decided to make it his permanent home, and he started what would become the oldest English settlement in Maryland. Ever since then Kent Island has thrived as the crossroads of the Chesapeake. Several people, from founding fathers en route between Annapolis and Philadelphia, to vacationers on their way to Ocean City, have visited the island. Many of them, like Claiborne, have even liked Kent Island so much that they decided to move there.

By car

From Washington, take U.S. 50 east towards Annapolis, or if you're coming from the Baltimore area, take I-97 south to U.S. 50 east. Then, from Annapolis, follow U.S. 50 east towards the Bay Bridge (toll for the bridge is $4 eastbound only, as of July 2019). After crossing the bridge, you're there! Exits 37 and 41 provide access to the island's major tourist attractions.

By plane

• Bay Bridge Airport (FAA:w29) is a small, regional airport with no scheduled commercial flights. Private planes park within walking distance of Hemmingway's restaurant and Kent Island Depot (a deli). Taxis, rental cars, aircraft rental, flight training, and aircraft maintenance are available
• Kentmorr Airpark (FAA:3W3) http://www.3w3.us/ is a small grass airstrip with no scheduled commercial flights. Private planes park within walking distance of the Kentmorr Restaurant & Crabhouse and the Kentmorr Marina. Cab transportation to town is also available.

The main way to get around Kent Island is by car, at least for now. Routes 8, 18, and 50 are the main roads to take from place to place, but if you want to go on foot or on bike, you can use the hiker-biker trails. The Cross Island Trail, as its name implies, goes across the island from Terrapin Park to Kent Narrows, and the Kent Island South Trail goes from Matapeake Park to Romancoke Pier. The trails unfortunately do not connect with each other, but there are plans to fix that in the future along with another trail south of Route 50, connecting Kent Narrows with Chester. With the new trails, future trips to Kent Island may involve getting around by bike instead of by car, just be ready for the workout; Kent Island already has over 12 miles of trail!

• Historic Stevensville, along the southern part of Love Point Road and East Main Street in Stevensville. Kent Island's historic downtown area has restored historic buildings, preserving its 19th-century small-town feel. The area also offers shopping and dining. To get there, take Exit 37 to Route 8 north, then follow the signs to Stevensville and Historic Stevensville.
• Terrapin Park, off Skipjack Parkway in Stevensville. A nature park that offers beautiful views of nature, the Chesapeake Bay, and the Bay Bridge. To get there, take Exit 37 to Route 8 north, turn left onto Skipjack Parkway, then turn left onto Bateau Drive.

• Chesapeake Bay Bridge WalkChesapeake Bay Bridge. The Bay Bridge Walk offers a unique opportunity to take a 4.3-mile walk across the Chesapeake Bay Bridge, the longest bridge in Maryland. The walk is usually held the first Sunday of May, but it's not held every year, so check in advance.

• Chesapeake Chocolates

  address: 202 Island Plaza

• Annie's Paramount Steak House

  address: 500 Kent Narrows Way N, Grasonville
  Also serves seafood.

• Fisherman's Inn and Crab Deck

  phone: +1 410 827-6666 (crab deck), +1 410 827-8807 (restaurant)
  address: 316 Main St, Grasonville

• Hemmingway's

  address: 357 Pier One Road, Stephensville

• Kentmorr Restaurant and Crab House

  address: 910 Kentmorr Road, Stevensville
  Offers inside and outside dining and also features both inside and outside bars. There is a nice sandy beach behind the restaurant, open to public.

• Rustico Restaurant

  address: 401 Love Point Road
  Italian

• No Place Bar Love Point Rd, Stevensville.

• Ram's Head Shore House

  phone: +1 410 643-2466
  address: 800 Main Street, Stevensville

• Red Eyes Dock Bar

  phone: +1 410 827-EYES
  address: Kent Narrows, Grasonville

• The Big Owl Tiki Bar

  phone: +1 410 827-6523
  address: 3015 Kent Narrows Way South, Grasonville

• Comfort Inn

  address: 3101 Main Street, Grasonville

• Hilton Garden Inn

  phone: +1 410 827-3877
  address: 3206 Main Street, Grasonville

• Holiday Inn Express

  address: 1020 Kent Narrows Rd. Grasonville

• Kent Manor Inn

  address: 500 Kent Manor Drive, Stevensville
  (for lodging). A pricey, yet beautiful, country inn just off of Route 8 near the Bay Bridge Airport, and across Route 50 from Historic Stevensville. Nice restaurant, too.

• Kent Island Beach House

  phone: +1 410-984-7618
  address: Stevensville MD

When on Kent Island, Verizon and Sprint/Nextel get the best service (Telus/Bell for Canadians, they work just as well), AT&T/T-Mobile (Rogers/Fido) get poor to no service, especially on the southern end. Check with your wireless carrier (or your roaming partner if you are travelling) for any changes. You can expect better over all service from any carrier the closer you are to Annapolis (especially AT&T).

Annapolis and Cape St. Claire are on the other side of the Bay Bridge, and Grasonville, Centreville, and Wye Mills are on the other side of the Kent Narrows Bridge. Grasonville is immediately past the bridge and beyond it lies Queenstown, the location of the Queenstown Prime Outlets which offer designer outlet shopping. Beyond Queenstown you have a choice of going north along Route 301 to Centreville and the upper counties, and southeast along Route 50 to Wye Mills and the lower shore. You can also go to Baltimore or Washington, D.C., home to historical places, national monuments, museums, aquariums, and the U.S. Capitol Building and the White House.